Windward Vacation Packages

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Top Holiday Package Deals in Windward

Price found within the past 48 hours. Click for updated prices.

The Landon Bay Harbor - Miami Beach

Save 100% on your flight

CA $1,076

per person

Nov 26 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

8.4/10 Very good! (1,003 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $12,917

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Shore View Hotel

Hollywood Beach

Save 100% on your flight

CA $1,196

per person

Nov 26 - Dec 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.4/10 Exceptional! (49 reviews)

Room was not clean- kitchen sink in particular was filthy. Check in was terrible- no one at the office, stood outside for 45 mins waiting for someone to answer the phone. Would not stay here again.

Reviewed on Apr 27, 2026

Private Oasis at Arya

Coconut Grove

Save 100% on your flight

CA $1,152

per person

Nov 7 - Nov 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.6/10 Excellent! (1,034 reviews)

The hotel is very beautiful, i'll give it that. The location was okay, though it was a little far from a lot of the places we were going. But I have to be honest about the housekeeping, because this really bothered me. When I pulled back the comforter to get into bed, there was makeup on the sheets they clearly had not been washed. I called to ask for fresh sheets, and when someone finally came, they didn't even change them. They just flipped the same sheet around, I know because I checked the bottom of the sheet. That was honestly disgusting, and I was very upset. I tried not to let it ruin the trip with my sister, but clean sheets are the bare minimum. Beautiful property, but this needs to be fixed."

Reviewed on Sep 23, 2026

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

CA $1,720

per person

Dec 10 - Dec 16

found 7 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

9/10 Wonderful! (83 reviews)

Amazing

Reviewed on Sep 21, 2026

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward

A beach with clear turquoise water, a rocky shoreline, and several high-rise buildings in the background.

South Beach

2 out of top 10 points of interest in this area

Major entertainment destination with numerous nightclubs, restaurants, and boutiques. Stroll along Lincoln Road and Ocean Drive, admire Art Deco buildings, and enjoy easy access to public transportation.

A coastal cityscape with high-rise buildings and a marina.

Brickell

1 out of top 10 points of interest in this area

A dense, high-rise residential area with upscale condos, Brickell boasts popular Miami restaurants, shops, and art galleries. Explore Mary Brickell Village or catch the Metromover for easy transportation.

A city skyline at dusk with illuminated buildings reflecting on the water.

Downtown Miami

2 out of top 10 points of interest in this area

An urban city center with a rich cultural scene, Downtown Miami offers shopping at Flagler Street, Bayside Marketplace, and Mary Brickell Village. Explore Pérez Art Museum Miami, Miami Children's Museum, and enjoy the pedestrian-friendly area with extensive public transit options.

A modern urban area with two prominent high-rise buildings, a central road, and surrounding commercial buildings.

Doral

A noteworthy feature of Doral is its popular shops. While you're in town, be sure to stop and check out CityPlace Doral and Miami International Mall.

A street with palm trees, cars, and a pedestrian crossing sign.

Flamingo/Lummus

If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and Miami Beach Boardwalk are top sights worth seeing.

Windward Hotel Deals

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $416

CA $569 total

Sep 27 - Sep 28

includes taxes & fees

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $364

CA $495 total

Oct 1 - Oct 2

includes taxes & fees

Miami International Airport Hotel

N.W. 20th & Lejeune Road Miami FL

Fully refundableReserve now, pay when you stay

CA $225

CA $254 total

Sep 27 - Sep 28

includes taxes & fees

8/10 Very good! (5,655 reviews)

"1"

Reviewed on Sep 23, 2026

See all 23,872 properties in Windward

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.